Encyclopedia / Organic Intermediate / Pharmaceutical Intermediates / Other Chemicals

tert-Butyldimethylsilyl chloride

CAS：18162-48-6
MW:150.7218
MF：C6H15ClSi

Tert-Butyldimethylsilyl chloride, with the chemical formula C6H15ClSi and CAS registry number 18162-48-6, is a compound commonly used in organic synthesis. This colorless liquid, also known as TBDMS chloride, is characterized by its tert-butyldimethylsilyl group and chloride functional group. It is often used as a protecting group for alcohols and a reagent for the introduction of the tert-butyldimethylsilyl moiety into various molecules. TBDMS chloride is compatible with a wide range of reaction conditions and is widely utilized in the preparation of pharmaceuticals, agrochemicals, and other organic compounds.

View more+

Email Tweet Share

Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: tert-Butyldimethylsilyl chloride

1.2 Synonyms: BDCS; Butyldimethylsilyl chloride; CB2790; Chloro(dimethyl)(2-methyl-2-propanyl)silane; EINECS 242-042-4; MFCD00000501; SILANE TBM2; SILANE, CHLORO(1,1-DIMETHYLETHYL)DIMETHYL-; Silane, chloro-tert-butyldimethyl-; Silane, t-butylchlorodimethyl-; TBDMCl; TBDMCS; TBDMS chloride; tbdmschloride; TBDMSCI; TBDMSCl; TBSCL; TBUME2SI-CL; t-butyl dimethyl chlorsilane; t-butylchlorodimethyl-silan; T-BUTYLDIMENHYLSILYL CHLORIDE; T-BUTYLDIMETHYLCHLOROSILANE; T-BUTYLDIMETHYLSILYL CHLORIDE; tert-butyl(chloro)dimethylsilane; tert-Butyl(chloro)dimethylsilane,tert-Butyldimethylchlorosilane,TBDMSCl; tert-Butylchlorodimethylsilane; tert-Butyldim; tert-Butyldimethylchlorosilane; tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]; tert-Butyldimethylsilyl chloride; tert-butyldimethylsilylchloride;

View all

1.3 CAS No.: 18162-48-6

1.4 CID: 28928

1.5 EINECS: 242-042-4

1.6 Molecular Formula: C6H15ClSi

1.7 Inchi: InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3

1.8 InChkey: BCNZYOJHNLTNEZ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)(C)[Si](C)(C)Cl

1.10 Isomers Smiles: CC(C)(C)[Si](C)(C)Cl

2. Properties

2.1 Appearance: White solid

2.2 Storage: Moisture Sensitive. Ambient temperatures.

2.3 Chemical Properties: White solid

2.4 Color/Form: Clear colorless

2.5 Water Solubility: Insoluble

2.6 Stability: Stable under normal temperatures and pressures.

2.7 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Definition: ChEBI: A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry aplications.

3.2 Description

Tert-Butyldimethylsilyl chloride, with the chemical formula C6H15ClSi, has the CAS number 18162-48-6. It is a colorless liquid with a pungent odor. The basic structure of tert-Butyldimethylsilyl chloride consists of a tert-butyl group, two methyl groups, a chlorine atom, and a silicon atom. This compound is soluble in organic solvents such as dichloromethane and chloroform. However, it is insoluble in water. Safety information indicates that tert-Butyldimethylsilyl chloride may cause skin and eye irritation. It is also harmful if swallowed or inhaled. Therefore, proper precautions should be taken when handling this chemical. It is important to avoid exposure to high temperatures or open flames, as tert-Butyldimethylsilyl chloride may emit toxic fumes. Overall, tert-Butyldimethylsilyl chloride should be handled with care to ensure safety.

Applicable Fields

Organic Synthesis: tert-Butyldimethylsilyl chloride is commonly used in organic synthesis as a protecting group for alcohols and amines. Its purpose in this field is to selectively protect certain functional groups during chemical reactions, preventing unwanted reactions from occurring. The mechanism of action involves the formation of a stable silyl ether or silylamine, which can be easily removed under specific conditions.

Pharmaceutical Industry: This compound finds applications in the pharmaceutical industry as a reagent for the synthesis of various pharmaceutical compounds. It is used to introduce tert-butyldimethylsilyl (TBDMS) groups into molecules, which can enhance their stability and facilitate further chemical modifications. The mechanism of action in this context is similar to its use in organic synthesis, where tert-Butyldimethylsilyl chloride acts as a protecting group.

Storage

Conditions: Store in a cool and dry place.

View all

3.3 Purification Methods: Fractionally distil it at atmospheric pressure. [Sommer & Tyler J Am Chem Soc 76 1030 1954, Corey & Venkateswarlu J Am Chem Soc 94 6190 1972, Beilstein 4 IV 4076.] tert-Butyldimethylsilyl chloride Preparation Products And Raw materials Preparation Products

View all

3.4 Usage: Used to protect alcohols during organic synthesis.

4. Safety and Handling

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of Cl^?.
Hazard Codes of tert-Butylchlorodimethylsilane (CAS NO.18162-48-6): C, F, T
Risk Statements: 35-40-34-10-19-11-67-65-63-48-20/21/22-45-23/24/25?
R11:Highly flammable.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R34:Causes burns.?
R35:Causes severe burns.?
R40:Limited evidence of a carcinogenic effect.?
R45:May cause cancer.?
R63:Possible risk of harm to the unborn child.?
R65:Harmful: may cause lung damage if swallowed.?
R67:Vapours may cause drowsiness and dizziness.
Safety Statements: 26-36/37/39-46-62-45-25-16-28-27-33-29-53?
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
16: Keep away from sources of ignition - No smoking.;
25: Avoid contact with eyes.;
36/37/39: Wear suitable protective clothing, gloves and eye/face protection.;
46:?If swallowed, seek medical advice immediately and show this container or label??
62:? If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label?
45:In case of accident of if you feel unwell, seek medical advice immediately (show the label where possible).;
27:?Take off immediately all contaminated clothing?
F 10-21:?Keep under argon. Sensitive to humidity.
Hazard Note: Flammable/Corrosive/Moisture Sensitive
RIDADR: UN 2925 4.1/PG 2
HazardClass: 4.1
WGK Germany: 2

View all

4.3 Sensitive: Moisture Sensitive

4.4 Specification: ?tert-Butylchlorodimethylsilane is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product:?Do not induce vomiting. Get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, tert-Butylchlorodimethylsilane (CAS NO.18162-48-6) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, alkali metals, aluminum, and you must not take it with incompatible materials, ignition sources, heat. And also prevent it to broken down into hazardous decomposition products:?Hydrogen chloride, carbon monoxide, carbon dioxide, silicon dioxide, phosgene gas.

View all

4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	1gm/kg (1000mg/kg)	IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE	Personal Communication from G.D. Stoner, Dept. of Community Medicine, School of Medicine, Univ. of California, La Jolla, CA 92037, May 25, 1975Vol. 27MAY1975,

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

IR : liquid film

Mass spectrum (electron ionization)

7. Synthesis Route

18162-48-6Total: 20 Synthesis Route

75-78-5 7 Suppliers

18162-48-6 404 Suppliers

2357-76-8

18162-48-6 404 Suppliers

View all

8. Precursor and Product

precursor:

594-19-4

75-78-5

2357-76-8

18159-55-2

507-20-0

18163-07-0

18173-64-3

29681-57-0

72726-46-6

66548-21-8

product:

80594-86-1

77744-44-6

76358-53-7

88339-93-9

67875-55-2

41879-37-2

97315-18-9

56522-24-8

18052-27-2

41879-39-4

9. Computed Properties

Molecular Weight：150.7218g/mol
Molecular Formula：C₆H₁₅ClSi
Compound Is Canonicalized：True
XLogP3-AA：150.0631547
Monoisotopic Mass：150.0631547
Complexity：81
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：8
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBgAAgEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGBAAAAAgDACAIABCAAAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

BRN: 505999

Introduction: Triethylchlorosilane is a clear, colourless to yellowish, pungent smelling, caustic and flammable liquid. It can be dissolved in non-protonating solvents without decomposition.
It may be used as silylating agent for dervatization of primary and secondary alcohols etc.. Also it may be used to protect allylic esters as silylketene acetal which is ore stable but less volatile derivates than trimethylchlorosilane.

View all

Chemical Properties: White solid

Uses: Used to protect alcohols during organic synthesis.

Definition: ChEBI: A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry ap lications.

Hazard: Moderately toxic.

Purification Methods: Fractionally distil it at atmospheric pressure. [Sommer & Tyler J Am Chem Soc 76 1030 1954, Corey & Venkateswarlu J Am Chem Soc 94 6190 1972, Beilstein 4 IV 4076.]

Usage: tert-Butyldimethylchlorosilane is used to protect hydroxyl group in organic synthesis. It finds application in the synthesis of prostaglandin. It is also used as an auxiliary material for hypolipaemics such as lovastatin and simvastatin. It plays an important role in the preparation of isoxazolines N-oxides from alpha-bromonitroalkanes. It acts as a versatile protecting reagent for amines, amides and alcohols.

View all

Chemical Properties: tert-Butyldimethylsilyl chloride is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols.It is an organosilicon compound that can be used as a versatile protecting reagent for alcohols, amines, amides, and various carboxylic acids.

Uses: t-Butyldimethylchlorosilane is useful as an anion trapping reagent. For example, TBDMSCl was found to be an efficient trap of the lithio α-phenylthiocyclopropane anion.When dichlorothiophene was treated with 2 equiv of n-butyllithium followed by 2 equiv of TBDMSCl the di-TBDMS-thiophene was isolated. The lithium anions of primary (eq 1) and secondary (eq 2) nitriles were trapped with TBDMSCl to give C,N-disilyl- and Nsilylketenimines in excellent yields.
Silyl stannanes have been prepared by trapping tin anions with TBDMSCl or other silyl chlorides. Alkynes treated with silyl stannanes and catalytic tetrakis(triphenylphosphine)palladium(0) give cis-silyl stannylalkenes in good yields.

View all

Preparation: tert-butyldimethylsilyl chloride (TBSCI, mp 86–89 °C) is expensive though it is readily prepared in high yield by the reaction of tert-butyllithium with dichlorodimethylsilane.

Definition: ChEBI: Tert-butyldimethylsilyl chloride is a silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry applications. It has a role as a chromatographic reagent.

View all

Reactions: tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ethers:(Me3C)Me2SiCl + ROH → (Me3C)Me2SiOR + HCl
These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers.

Purification Methods: Fractionally distil it at atmospheric pressure. [Sommer & Tyler J Am Chem Soc 76 1030 1954, Corey & Venkateswarlu J Am Chem Soc 94 6190 1972, Beilstein 4 IV 4076.]

11. Toltal 381 Suppliers View more

High quality tert-Butyldimethylsilyl chloride CAS 18162-48-6 in stock

Tianjin Furun Tongda International Trade Co., LTD

^1YR

Tel: Update Time:2024/11/15

inquire

Hebei Yanxi Chemical Co.,Ltd

^1YR

Tel: Update Time:2024/11/14

inquire

High purity tert-Butyldimethylsilyl chloride CAS 18162-48-6 with fast delivery

Wuhan Fortuna Chemical Co., Ltd.

^1YR

Tel: Update Time:2024/08/08

inquire

Baoji Guokang Healthchem co.,ltd

^1YR

Tel: Update Time:2024/11/15

inquire

CANGZHOU ENKE PHARMA-TECH CO.,LTD

^1YR

Tel: Update Time:2024/11/12

inquire

12. Related Questions

: How to Prepare tert-Butyldimethylsilyl Chloride?Background Technology tert-Butyldimethylsilyl chloride, also known as Tert-butyl dimethly chlorosilane, with the molecular formula t-C4H9(CH3)2SiCl, appears as white transparent crystals with a boilin..; What are the uses and potential health effects of tert-Butyldimethylsilyl chloride?Description Tert-butyldimethylsilyl chloride (TBDMSCl) is a silyl chloride compound with a central silicon atom covalently bound to one chloro, one tert-butyl, and two methyl groups. It is commonly us..; What is tert-Butyldimethylsilyl chloride and its Applications?What is tert-Butyldimethylsilyl chloride? tert-Butyldimethylsilyl chloride (TBDMSCL) is a commonly used protectant in organic synthesis. It effectively protects the hydroxyl functionality by transform..; How to Synthesize tert-Butyldimethylsilyl Chloride? Tert-Butyldimethylsilyl chloride, also known as tert-butyl dimethly chlorosilane, is a white transparent crystalline substance with a boiling point of 124°C - 126°C and a melting point of 87°C - 90°C..

13. Realated Product Infomation